NPASS Compound

Structure

NPC117980 OpenBabel07101718322D 35 41 0 0 1 0 0 0 0 0999 V2000 0.8286 -0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0233 1.1841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1573 1.6841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4804 0.4801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2183 0.7445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8894 2.6841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8209 4.2668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1183 3.4699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9314 1.3231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8884 0.5129 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8894 1.6841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8137 0.8921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1573 2.6841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4142 3.3533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5185 2.6697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0233 3.1841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4716 1.4862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0941 1.8520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5203 2.7295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4360 3.1453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0497 2.1468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1489 1.9864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7669 3.8885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9556 -0.2948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0150 0.9999 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7554 1.1841 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.2788 -1.2411 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8154 4.1623 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.0646 3.1466 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5312 0.5230 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1270 2.1943 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.2113 3.6806 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.4645 1.6056 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0759 4.8395 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 3 2 0 0 0 0 2 11 1 0 0 0 0 3 13 1 0 0 0 0 4 5 2 0 0 0 0 4 12 1 0 0 0 0 5 17 1 0 0 0 0 6 11 2 0 0 0 0 6 16 1 0 0 0 0 7 14 2 0 0 0 0 7 28 1 0 0 0 0 8 15 2 0 0 0 0 8 29 1 0 0 0 0 9 30 1 0 0 0 0 10 12 1 0 0 0 0 10 25 1 1 0 0 0 11 26 1 0 0 0 0 12 18 2 0 0 0 0 13 14 1 0 0 0 0 13 16 2 0 0 0 0 14 20 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 0 0 0 0 16 28 1 0 0 0 0 17 21 2 0 0 0 0 17 34 1 0 0 0 0 18 21 1 0 0 0 0 19 22 2 0 0 0 0 19 32 1 0 0 0 0 20 23 1 0 0 0 0 20 31 2 0 0 0 0 21 29 1 0 0 0 0 22 25 1 0 0 0 0 22 31 1 0 0 0 0 23 32 1 0 0 0 0 23 35 2 0 0 0 0 24 27 2 0 0 0 0 24 30 1 0 0 0 0 24 33 1 0 0 0 0 25 9 1 6 0 0 0 25 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	529.09
Volume:	463.265
LogP:	3.597
LogD:	2.336
LogS:	-5.842
# Rotatable Bonds:	1
TPSA:	147.97
# H-Bond Aceptor:	9
# H-Bond Donor:	7
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.195
Synthetic Accessibility Score:	4.868
Fsp3:	0.16
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.716
MDCK Permeability:	3.83971564588137e-06
Pgp-inhibitor:	0.534
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.602
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.389

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	99.22822570800781%
Volume Distribution (VD):	0.602
Pgp-substrate:	0.8887362480163574%

ADMET: Metabolism

CYP1A2-inhibitor:	0.914
CYP1A2-substrate:	0.666
CYP2C19-inhibitor:	0.566
CYP2C19-substrate:	0.047
CYP2C9-inhibitor:	0.81
CYP2C9-substrate:	0.661
CYP2D6-inhibitor:	0.889
CYP2D6-substrate:	0.798
CYP3A4-inhibitor:	0.839
CYP3A4-substrate:	0.133

ADMET: Excretion

Clearance (CL):	5.174
Half-life (T1/2):	0.495

ADMET: Toxicity

hERG Blockers:	0.645
Human Hepatotoxicity (H-HT):	0.359
Drug-inuced Liver Injury (DILI):	0.964
AMES Toxicity:	0.828
Rat Oral Acute Toxicity:	0.98
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.304
Carcinogencity:	0.137
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.978

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC117980

Natural Product ID:	NPC117980
*Common Name:**	Dragmacidin E
IUPAC Name:	n.a.
Synonyms:	Dragmacidin E
Standard InCHIKey:	ZUCSTWKVHHAHLA-REFGNXHDSA-N
Standard InCHI:	InChI=1S/C25H20BrN7O2/c1-10-12-4-5-17(34)21-18(12)15(8-29-21)19-22(25(10)9-30-24(27)33-25)31-20(23(35)32-19)14-7-28-16-6-11(26)2-3-13(14)16/h2-8,10,28-29,34H,9H2,1H3,(H,32,35)(H3,27,30,33)/t10-,25-/m1/s1
SMILES:	N=C1NC[C@]2(N1)c1nc(c(=O)[nH]c1c1c3c([C@H]2C)ccc(c3[nH]c1)O)c1c[nH]c2c1ccc(c2)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL472439
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0004162] Hydroxyindoles

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921415]
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16154746]
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253840]
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	southern australian	n.a.	PMID[9599272]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	22.0	ppm	PMID[548886]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	36.0	ppm	PMID[548886]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC117980 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	791
0.1-0.2	5951
0.2-0.3	12367
0.3-0.4	16710
0.4-0.5	3233
0.5-0.6	2574
0.6-0.7	982
0.7-0.8	87
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9449	High Similarity	NPC475746
0.7942	Intermediate Similarity	NPC477608
0.7866	Intermediate Similarity	NPC477609
0.7796	Intermediate Similarity	NPC477607
0.7778	Intermediate Similarity	NPC167908
0.7773	Intermediate Similarity	NPC477610
0.7744	Intermediate Similarity	NPC77101
0.7738	Intermediate Similarity	NPC201831
0.7738	Intermediate Similarity	NPC17487
0.7708	Intermediate Similarity	NPC477108
0.7708	Intermediate Similarity	NPC477107
0.7708	Intermediate Similarity	NPC477109
0.764	Intermediate Similarity	NPC325976
0.7572	Intermediate Similarity	NPC475736
0.75	Intermediate Similarity	NPC264285
0.749	Intermediate Similarity	NPC63031
0.748	Intermediate Similarity	NPC326363
0.7461	Intermediate Similarity	NPC171393
0.7461	Intermediate Similarity	NPC295452
0.7453	Intermediate Similarity	NPC315467
0.7373	Intermediate Similarity	NPC268744
0.7373	Intermediate Similarity	NPC153123
0.7373	Intermediate Similarity	NPC201266
0.7373	Intermediate Similarity	NPC220797
0.7373	Intermediate Similarity	NPC474318
0.7373	Intermediate Similarity	NPC475914
0.7371	Intermediate Similarity	NPC156003
0.7368	Intermediate Similarity	NPC474195
0.7362	Intermediate Similarity	NPC245055
0.7361	Intermediate Similarity	NPC478009
0.7342	Intermediate Similarity	NPC205254
0.7342	Intermediate Similarity	NPC269203
0.7342	Intermediate Similarity	NPC303820
0.7342	Intermediate Similarity	NPC13456
0.7342	Intermediate Similarity	NPC106771
0.7342	Intermediate Similarity	NPC166209
0.7342	Intermediate Similarity	NPC77241
0.7342	Intermediate Similarity	NPC23420
0.7339	Intermediate Similarity	NPC473317
0.7338	Intermediate Similarity	NPC314882
0.7326	Intermediate Similarity	NPC473312
0.732	Intermediate Similarity	NPC474196
0.7311	Intermediate Similarity	NPC475935
0.7311	Intermediate Similarity	NPC94211
0.7311	Intermediate Similarity	NPC52909
0.7309	Intermediate Similarity	NPC16352
0.7305	Intermediate Similarity	NPC15801
0.7295	Intermediate Similarity	NPC128084
0.7293	Intermediate Similarity	NPC478006
0.7282	Intermediate Similarity	NPC315499
0.7256	Intermediate Similarity	NPC63109
0.7251	Intermediate Similarity	NPC125597
0.7237	Intermediate Similarity	NPC28945
0.7235	Intermediate Similarity	NPC471536
0.7232	Intermediate Similarity	NPC478010
0.7229	Intermediate Similarity	NPC276657
0.7228	Intermediate Similarity	NPC74619
0.7222	Intermediate Similarity	NPC24370
0.7222	Intermediate Similarity	NPC214142
0.7222	Intermediate Similarity	NPC319232
0.7208	Intermediate Similarity	NPC476073
0.72	Intermediate Similarity	NPC314176
0.7194	Intermediate Similarity	NPC118559
0.7194	Intermediate Similarity	NPC124920
0.7194	Intermediate Similarity	NPC261251
0.7194	Intermediate Similarity	NPC34580
0.7194	Intermediate Similarity	NPC304307
0.7191	Intermediate Similarity	NPC477167
0.7191	Intermediate Similarity	NPC473342
0.7191	Intermediate Similarity	NPC304187
0.7191	Intermediate Similarity	NPC477166
0.7177	Intermediate Similarity	NPC477114
0.717	Intermediate Similarity	NPC153400
0.7165	Intermediate Similarity	NPC100547
0.7164	Intermediate Similarity	NPC478011
0.7154	Intermediate Similarity	NPC207020
0.7137	Intermediate Similarity	NPC95240
0.7137	Intermediate Similarity	NPC322135
0.7137	Intermediate Similarity	NPC223409
0.7115	Intermediate Similarity	NPC37152
0.7109	Intermediate Similarity	NPC14288
0.7108	Intermediate Similarity	NPC293151
0.7104	Intermediate Similarity	NPC184225
0.7104	Intermediate Similarity	NPC285343
0.7101	Intermediate Similarity	NPC321939
0.7096	Intermediate Similarity	NPC314056
0.7093	Intermediate Similarity	NPC33064
0.7093	Intermediate Similarity	NPC97902
0.7083	Intermediate Similarity	NPC476167
0.7082	Intermediate Similarity	NPC54803
0.7082	Intermediate Similarity	NPC279189
0.7082	Intermediate Similarity	NPC200553
0.7082	Intermediate Similarity	NPC321592
0.7078	Intermediate Similarity	NPC473376
0.7077	Intermediate Similarity	NPC82472
0.7077	Intermediate Similarity	NPC41679
0.7075	Intermediate Similarity	NPC130570
0.7068	Intermediate Similarity	NPC142901
0.7057	Intermediate Similarity	NPC477633
0.7054	Intermediate Similarity	NPC220852
0.7054	Intermediate Similarity	NPC284888
0.7054	Intermediate Similarity	NPC213308
0.7054	Intermediate Similarity	NPC323752
0.705	Intermediate Similarity	NPC477861
0.7046	Intermediate Similarity	NPC99666
0.7045	Intermediate Similarity	NPC82370
0.7045	Intermediate Similarity	NPC178858
0.7043	Intermediate Similarity	NPC476451
0.7042	Intermediate Similarity	NPC192315
0.7042	Intermediate Similarity	NPC131887
0.7042	Intermediate Similarity	NPC474389
0.704	Intermediate Similarity	NPC478012
0.7036	Intermediate Similarity	NPC470501
0.7029	Intermediate Similarity	NPC222018
0.7019	Intermediate Similarity	NPC471891
0.7018	Intermediate Similarity	NPC478013
0.7016	Intermediate Similarity	NPC207686
0.7008	Intermediate Similarity	NPC51388
0.7	Intermediate Similarity	NPC162002
0.7	Intermediate Similarity	NPC74969
0.7	Intermediate Similarity	NPC477549
0.7	Intermediate Similarity	NPC227582
0.6996	Remote Similarity	NPC470502
0.6992	Remote Similarity	NPC323244
0.6983	Remote Similarity	NPC315491
0.6983	Remote Similarity	NPC45459
0.698	Remote Similarity	NPC175602
0.6974	Remote Similarity	NPC216369
0.6966	Remote Similarity	NPC477635
0.6966	Remote Similarity	NPC477630
0.6964	Remote Similarity	NPC61038
0.6962	Remote Similarity	NPC174489
0.6948	Remote Similarity	NPC110182
0.6944	Remote Similarity	NPC477714
0.6944	Remote Similarity	NPC303658
0.6941	Remote Similarity	NPC470503
0.6939	Remote Similarity	NPC475070
0.6935	Remote Similarity	NPC5145
0.6929	Remote Similarity	NPC77555
0.692	Remote Similarity	NPC54744
0.6914	Remote Similarity	NPC245348
0.6914	Remote Similarity	NPC252338
0.6908	Remote Similarity	NPC26641
0.6905	Remote Similarity	NPC476041
0.6905	Remote Similarity	NPC304926
0.6904	Remote Similarity	NPC324149
0.6895	Remote Similarity	NPC162860
0.6895	Remote Similarity	NPC80596
0.6887	Remote Similarity	NPC60006
0.6885	Remote Similarity	NPC328924
0.6885	Remote Similarity	NPC132329
0.6883	Remote Similarity	NPC54420
0.688	Remote Similarity	NPC78609
0.688	Remote Similarity	NPC470702
0.688	Remote Similarity	NPC473218
0.688	Remote Similarity	NPC6865
0.688	Remote Similarity	NPC153980
0.6877	Remote Similarity	NPC181081
0.6877	Remote Similarity	NPC469717
0.6875	Remote Similarity	NPC229893
0.6873	Remote Similarity	NPC477176
0.6873	Remote Similarity	NPC470729
0.687	Remote Similarity	NPC272549
0.687	Remote Similarity	NPC470500
0.6865	Remote Similarity	NPC322064
0.6864	Remote Similarity	NPC308931
0.6864	Remote Similarity	NPC99939
0.6853	Remote Similarity	NPC282247
0.6853	Remote Similarity	NPC470703
0.6853	Remote Similarity	NPC207866
0.685	Remote Similarity	NPC292958
0.685	Remote Similarity	NPC269270
0.6849	Remote Similarity	NPC207620
0.6848	Remote Similarity	NPC242872
0.6848	Remote Similarity	NPC263117
0.6848	Remote Similarity	NPC125181
0.6846	Remote Similarity	NPC474877
0.6846	Remote Similarity	NPC474701
0.6842	Remote Similarity	NPC476121
0.684	Remote Similarity	NPC72956
0.6838	Remote Similarity	NPC27041
0.6838	Remote Similarity	NPC53534
0.6838	Remote Similarity	NPC477715
0.6836	Remote Similarity	NPC220851
0.6831	Remote Similarity	NPC171317
0.6829	Remote Similarity	NPC475774
0.6829	Remote Similarity	NPC476098
0.6827	Remote Similarity	NPC476116
0.6825	Remote Similarity	NPC478157
0.6824	Remote Similarity	NPC14686
0.6824	Remote Similarity	NPC272174
0.682	Remote Similarity	NPC935
0.682	Remote Similarity	NPC267078
0.6818	Remote Similarity	NPC242209
0.6816	Remote Similarity	NPC208522
0.6815	Remote Similarity	NPC270918
0.6809	Remote Similarity	NPC211416
0.6808	Remote Similarity	NPC69843
0.6808	Remote Similarity	NPC470730
0.6808	Remote Similarity	NPC477175

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC117980 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	368
0.1-0.2	668
0.2-0.3	1042
0.3-0.4	2457
0.4-0.5	2344
0.5-0.6	1906
0.6-0.7	358
0.7-0.8	7
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7714	Intermediate Similarity	NPD7603	Discontinued
0.7636	Intermediate Similarity	NPD8349	Phase 1
0.7572	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7148	Intermediate Similarity	NPD3746	Discontinued
0.7095	Intermediate Similarity	NPD4511	Phase 1
0.7071	Intermediate Similarity	NPD7948	Phase 1
0.7026	Intermediate Similarity	NPD6458	Discontinued
0.7017	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6165	Phase 2
0.6992	Remote Similarity	NPD6164	Phase 2
0.6983	Remote Similarity	NPD484	Approved
0.698	Remote Similarity	NPD4890	Phase 2
0.6942	Remote Similarity	NPD3814	Phase 1
0.6939	Remote Similarity	NPD5426	Phase 3
0.6883	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD8094	Discontinued
0.6846	Remote Similarity	NPD8106	Phase 2
0.684	Remote Similarity	NPD7470	Discontinued
0.684	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD8524	Approved
0.6823	Remote Similarity	NPD4442	Phase 2
0.6823	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD8093	Discontinued
0.6812	Remote Similarity	NPD6456	Discontinued
0.6805	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6999	Discontinued
0.6803	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD4558	Phase 2
0.6795	Remote Similarity	NPD4845	Discontinued
0.6783	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7781	Approved
0.6769	Remote Similarity	NPD7780	Approved
0.6758	Remote Similarity	NPD6242	Discontinued
0.6746	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD5901	Discontinued
0.672	Remote Similarity	NPD7666	Phase 3
0.672	Remote Similarity	NPD7665	Phase 2
0.6719	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7001	Phase 3
0.6702	Remote Similarity	NPD7181	Phase 3
0.668	Remote Similarity	NPD7717	Approved
0.668	Remote Similarity	NPD2794	Discontinued
0.668	Remote Similarity	NPD7716	Approved
0.6678	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7415	Suspended
0.6667	Remote Similarity	NPD2177	Approved
0.6667	Remote Similarity	NPD2176	Approved
0.6667	Remote Similarity	NPD7950	Approved
0.6667	Remote Similarity	NPD5612	Discontinued
0.6667	Remote Similarity	NPD7952	Approved
0.6667	Remote Similarity	NPD8292	Phase 2
0.6667	Remote Similarity	NPD7953	Approved
0.6667	Remote Similarity	NPD2175	Phase 3
0.6667	Remote Similarity	NPD7789	Approved
0.6667	Remote Similarity	NPD7790	Approved
0.6667	Remote Similarity	NPD7951	Approved
0.6667	Remote Similarity	NPD7689	Approved
0.6667	Remote Similarity	NPD7791	Approved
0.6654	Remote Similarity	NPD3809	Discontinued
0.6653	Remote Similarity	NPD6376	Discontinued
0.6653	Remote Similarity	NPD6664	Approved
0.6641	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.664	Remote Similarity	NPD5939	Approved
0.664	Remote Similarity	NPD5936	Approved
0.663	Remote Similarity	NPD3962	Phase 2
0.663	Remote Similarity	NPD3959	Phase 2
0.6624	Remote Similarity	NPD6595	Phase 3
0.6619	Remote Similarity	NPD7925	Phase 2
0.6619	Remote Similarity	NPD7924	Phase 2
0.6604	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD8016	Phase 3
0.6603	Remote Similarity	NPD7730	Approved
0.6603	Remote Similarity	NPD7731	Approved
0.6599	Remote Similarity	NPD8396	Approved
0.6599	Remote Similarity	NPD8395	Approved
0.6598	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.659	Remote Similarity	NPD7271	Approved
0.6587	Remote Similarity	NPD2916	Discontinued
0.6583	Remote Similarity	NPD6530	Approved
0.6583	Remote Similarity	NPD6531	Approved
0.6568	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7970	Approved
0.6553	Remote Similarity	NPD7824	Approved
0.655	Remote Similarity	NPD4429	Discontinued
0.6548	Remote Similarity	NPD6290	Phase 2
0.6545	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7726	Phase 1
0.6537	Remote Similarity	NPD7112	Discontinued
0.6532	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD2189	Approved
0.6522	Remote Similarity	NPD2187	Approved
0.6515	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD2813	Phase 3
0.6512	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.651	Remote Similarity	NPD4502	Phase 2
0.6498	Remote Similarity	NPD8442	Discontinued
0.6489	Remote Similarity	NPD6753	Phase 1
0.6489	Remote Similarity	NPD6752	Phase 1
0.6488	Remote Similarity	NPD706	Phase 1
0.6486	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD4548	Discontinued
0.6464	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD1038	Approved
0.6461	Remote Similarity	NPD3961	Discontinued
0.6455	Remote Similarity	NPD2951	Discontinued
0.6454	Remote Similarity	NPD6975	Discontinued
0.6453	Remote Similarity	NPD5559	Phase 2
0.6452	Remote Similarity	NPD2880	Discontinued
0.6451	Remote Similarity	NPD8525	Approved
0.645	Remote Similarity	NPD6995	Phase 1
0.6446	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD4885	Approved
0.6437	Remote Similarity	NPD7618	Phase 3
0.6437	Remote Similarity	NPD7619	Phase 3
0.6434	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6431	Remote Similarity	NPD8284	Discontinued
0.6431	Remote Similarity	NPD3006	Discontinued
0.6429	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5022	Discontinued
0.6426	Remote Similarity	NPD2803	Discontinued
0.642	Remote Similarity	NPD2411	Approved
0.642	Remote Similarity	NPD4852	Phase 2
0.6416	Remote Similarity	NPD6961	Discontinued
0.641	Remote Similarity	NPD7068	Approved
0.641	Remote Similarity	NPD7067	Approved
0.6406	Remote Similarity	NPD5116	Phase 1
0.6406	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6401	Remote Similarity	NPD6153	Approved
0.6398	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6388	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6388	Remote Similarity	NPD8356	Approved
0.6387	Remote Similarity	NPD5065	Approved
0.6382	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD8310	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7856	Phase 2
0.6374	Remote Similarity	NPD7857	Phase 3
0.6374	Remote Similarity	NPD7860	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD6473	Phase 1
0.637	Remote Similarity	NPD5891	Approved
0.6364	Remote Similarity	NPD8364	Approved
0.6364	Remote Similarity	NPD8363	Approved
0.636	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD6223	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD7558	Phase 2
0.6356	Remote Similarity	NPD996	Phase 2
0.6356	Remote Similarity	NPD994	Phase 2
0.6354	Remote Similarity	NPD3986	Discontinued
0.6354	Remote Similarity	NPD5482	Discontinued
0.6353	Remote Similarity	NPD8430	Approved
0.6337	Remote Similarity	NPD2096	Phase 2
0.6337	Remote Similarity	NPD2091	Phase 2
0.6337	Remote Similarity	NPD3872	Phase 3
0.6336	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD2616	Phase 3
0.6332	Remote Similarity	NPD2615	Phase 3
0.6328	Remote Similarity	NPD2442	Approved
0.6328	Remote Similarity	NPD2443	Approved
0.6326	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD5164	Discontinued
0.6319	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD4128	Approved
0.6318	Remote Similarity	NPD482	Approved
0.6316	Remote Similarity	NPD7711	Discontinued
0.6314	Remote Similarity	NPD6517	Phase 3
0.6314	Remote Similarity	NPD6716	Phase 1
0.6314	Remote Similarity	NPD2008	Discontinued
0.6312	Remote Similarity	NPD1996	Discontinued
0.6312	Remote Similarity	NPD6745	Discontinued
0.631	Remote Similarity	NPD6986	Phase 1
0.6306	Remote Similarity	NPD6969	Phase 2
0.6306	Remote Similarity	NPD6968	Phase 2
0.6306	Remote Similarity	NPD5479	Discontinued
0.6305	Remote Similarity	NPD7944	Discontinued
0.6304	Remote Similarity	NPD5807	Phase 2
0.6296	Remote Similarity	NPD2094	Phase 2
0.6296	Remote Similarity	NPD2095	Phase 2
0.6296	Remote Similarity	NPD2092	Phase 2
0.6296	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD4075	Phase 2
0.6291	Remote Similarity	NPD4440	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7923	Phase 2
0.6287	Remote Similarity	NPD4958	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data